A Novel Iron-catalyzed One-pot Synthesis of 3-Amino-1,2,4-triazoles

被引:9
|
作者
Rohand, Taoufik [1 ]
Mkpenie, Victor N. [2 ]
El Haddad, Mohammadine [1 ]
Marko, Istvan E. [3 ]
机构
[1] Cadi Ayyad Univ, Polydisciplinary Fac Safi, Lab Analyt & Mol Chem, Route SidiBouzid BP 4162, Marrakech 46000, Safi, Morocco
[2] Univ Uyo, Dept Chem, PMB 1017, Uyo, Nigeria
[3] Catholic Univ Louvain, Condensed Matter & Nanosci, Pl Louis Pasteur 1 Bte L4-01-02, B-1348 Louvain, Belgium
关键词
DERIVATIVES;
D O I
10.1002/jhet.3450
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel one-pot synthesis of 3-amino-1,2,4-triazole developed via iron (III) catalyzed route is reported. The new method is more efficient, simple, and convenient and presents a concise new strategy for the synthesis of 3-amino-1,2,4-triazole derivatives. The iron (III) complex intermediate assisted in the intramolecular bond cyclization owing to its Lewis acidity or oxidizing properties. A series of aromatic nitriles bearing different electron-donating and electron-withdrawing groups substituted at para and/or ortho positions were also investigated. The position of the substituents affected the yield of the final compound, with the para-substituted substrates giving relatively higher yields.
引用
收藏
页码:690 / 695
页数:6
相关论文
共 50 条
  • [31] Rapid, microwave-assisted synthesis of N1-substituted 3-amino-1,2,4-triazoles
    Meng, Jerry
    Kung, Pei-Pei
    TETRAHEDRON LETTERS, 2009, 50 (15) : 1667 - 1670
  • [32] CONDENSED HETEROCYCLES .4. CONDENSATION OF 3-AMINO-1,2,4-TRIAZOLES WITH DIACETONITRILE AND DIPROPIONITRILES
    LEVIN, YA
    KUKHTIN, VA
    JOURNAL OF GENERAL CHEMISTRY USSR, 1963, 33 (08): : 2608 - &
  • [33] Iron-Catalyzed One-Pot Oxidative Esterification of Aldehydes
    Wu, Xiao-Feng
    Darcelli, Christophe
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (08) : 1144 - 1147
  • [34] Study of the Two Steps and One-Pot Two-Step Mechanochemical Synthesis of Annulated 1,2,4-Triazoles
    Gonnet, Lori
    Andre-Barres, Christiane
    Guidetti, Brigitte
    Chamayou, Alain
    Menendez, Christophe
    Baron, Michel
    Calvet, Rachel
    Baltas, Michel
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (08) : 3114 - 3125
  • [35] One-Pot Domino Synthesis of 3-Amino-1,2-dihydroisoquinolines
    Hamri, W.
    Shyshkina, O. O.
    Tarasiuk, T. M.
    Volovnenko, T. A.
    Mesbah, K.
    Rhouati, S.
    Volovenko, Y. M.
    Medviediev, V. V.
    Shishkin, O. V.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (05) : 1373 - 1376
  • [36] Synthesis of 3,5-diaryl-4-benzylidene-amino-1,2,4-triazoles and 4-amino-3,5-diaryl-1,2,4-triazoles
    Zielinski W.
    Czardybon W.
    Chemistry of Heterocyclic Compounds, 2001, 37 (09) : 1107 - 1110
  • [37] Iron-catalyzed one-pot synthesis of benzimidazoles from 2-nitroanilines and benzylic alcohols
    Li, Gang
    Wang, Jin
    Yuan, Baokun
    Zhang, Dongfeng
    Lin, Ziyun
    Li, Peng
    Huang, Haihong
    TETRAHEDRON LETTERS, 2013, 54 (50) : 6934 - 6936
  • [38] ACIDITY,BASICITY AND TAUTOMERISM OF 3-AMINO-1,2,4-TRIAZOLES, 1,2,4-TRIAZOLONES AND 1,2,4-TRIAZOLETHIONES
    FREIBERG, W
    KROGER, CF
    ZEITSCHRIFT FUR CHEMIE, 1969, 9 (10): : 396 - &
  • [39] One-pot synthesis of 1,2,4-triazole-Fused heterocycles via sequential condensation and iron-catalyzed aerobic oxidation
    Wang, Linyang
    Huang, Xuxu
    Lan, Jinyun
    Wang, Jian
    TETRAHEDRON, 2024, 160
  • [40] Synthesis of Novel Derivatives of 1,2,4-Triazoles
    Galstyan, Armen S.
    Ghochikyan, Tariel, V
    Frangyan, Vardges R.
    Tamazyan, Rafael A.
    Ayvazyan, Armen G.
    CHEMISTRYSELECT, 2018, 3 (35): : 9981 - 9985